Structure determination and biosynthesis of a novel metabolite of Fusarium culmorum, apotrichodiol

• Published in: The Journal of biological chemistry Vol. 262; no. 32; pp. 15354 - 15358
• Main Authors: Zamir, L O, Devor, K A, Nadeau, Y, Sauriol, F
• Format: Journal Article
• Language: English
• Published: Bethesda, MD Elsevier Inc 15.11.1987; American Society for Biochemistry and Molecular Biology
• Subjects: Biological and medical sciences; BIOSINTESIS; BIOSYNTHESE; BIOSYNTHESIS; Chromatography, High Pressure Liquid; ESPECTROSCOPIA RMN; Fundamental and applied biological sciences. Psychology; FUSARIUM; Fusarium - metabolism; Fusarium culmorum; Growth, nutrition, metabolism, transports, enzymes. Molecular biology; Magnetic Resonance Spectroscopy; METABOLITE; METABOLITES; METABOLITOS; Mevalonic Acid - analogs & derivatives; Mevalonic Acid - metabolism; Microbiology; Mycology; NMR SPECTROSCOPY; Sesquiterpenes - biosynthesis; SPECTROSCOPIE RMN; Trichothecenes - biosynthesis; Fungi; Fusarium culmorum; Radiolabelling; Investigation method; Biosynthesis; Fungi Imperfecti; Metabolism; Thallophyta
• ISSN: 0021-9258; 1083-351X
• DOI: 10.1016/s0021-9258(18)47732-0

A novel dead-end metabolite of Fusarium culmorum was isolated and characterized (Zamir, L. O., and Devor, K. A. (1987) J. Biol. Chem. 15348-15353). This 3 alpha, 13-dihydroxy-apotrichothec-9-ene is herein given the trivial name of apotrichodiol to indicate its basic structure. The characterization of apotrichodiol was established through the application of spectroscopic techniques (ultraviolet, 1H-NMR, 13C-NMR, COSY, and DEPT experiments) on the natural product as well as on its diacetate derivative. The mode of folding of its precursor farnesyl pyrophosphate was derived from feeding experiments with 3,4-[13C2]mevalonolactone. 13C-NMR assignments were also made of 3-acetyldeoxynivalenol and sambucinol which were derived from these feedings with enriched mevalonolactone.